Tag: M.W=100-200

Application of 57561-39-4, A common heterocyclic compound, 57561-39-4, name is tert-Butyl (2-hydroxyethyl)(methyl)carbamate, molecular formula is C8H17NO3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL) and 4-dimethylaminopyridine (catalytic amount), and ethyl chlorocarbonate (1.25 mL) was dropwise added. The mixture was stirred overnight at room temperature and ethyl acetate (50 mL) was added. The mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride – ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.66 g) as a white solid.1H-NMR(DMSO-d6) : 1.23(3H,t,J=7.1Hz), 2.54 (3H,s), 3.16-3.22(2H,m), 4.15(2H,q,J=7.1Hz), 4.32-4.37(2H,m), 9.25 (2H,br).

The synthetic route of 57561-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1607088; (2005); A1;,
Amide – Wikipedia,
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Reference of 55512-05-5,Some common heterocyclic compound, 55512-05-5, name is 3-(Methylsulfonamido)benzaldehyde, molecular formula is C8H9NO3S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Under argon and at 0 C., 83 mg (0.417 mmol) of N-(3-formylphenyl)methanesulfonamide (Example 86A) were initially charged in 1 ml of abs. tetrahydrofuran. At 0 C., 99 mg (0.833 mmol) of methylmagesium bromide (3 M in diethyl ether) were added dropwise (resulting in the formulation of a precipitate), and the reaction solution was stirred at this temperature for 2 h. The reaction solution was quenched with water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Yield: 80 mg (89% of theory) LC-MS (Method 8): Rt=1.15 min; MS (ESIpos): m/z=214 [M-H]-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(Methylsulfonamido)benzaldehyde, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Vakalopoulos, Alexandros; Meibom, Daniel; Nell, Peter; Sussmeier, Frank; Albrecht-Kupper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Schneider, Dirk; Krenz, Ursula; US2013/210795; (2013); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 121492-06-6, name is N-Boc-(2-Aminoethyl)-N-methylamine, A new synthetic method of this compound is introduced below., Product Details of 121492-06-6

Step 1 [0216] A solution of N-Boc-N-methylethylenediamine (1 g, 5.74 mmol) and sulfamide (1.1 g, 11.48 mmol) in dioxane (20 mL) was stirred at reflux under N2 atmosphere (monitored by TLC). The mixture was then filtered to remove the insoluble material and the filtrate was concentrated under reduced pressure and treated with ethyl acetate. The insoluble material was again removed by filtration and the filtrate concentrated under reduced pressure to give the desired product in 96% yield.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; FOB SYNTHESIS; WO2005/123066; (2005); A1;,
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2227-79-4, name is Benzothioamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of Benzothioamide

A mixture of benzenecarbothioamide (6.86 g) , 1,3- dichloroacetone (6.35 g) and toluene (50 mL) was heated under reflux for 3 hr. The reaction mixture was cooled, and water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (9.77 g) . MS: [M+H]+ 210.1.

The synthetic route of 2227-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAJITA, Yuichi; MIKAMI, Satoshi; MIYANOHANA, Yuhei; KOIKE, Tatsuki; DAINI, Masaki; OYABU, Norio; OGINO, Masaki; TAKEUCHI, Kohei; ITO, Yoshiteru; TOKUNAGA, Norihito; SUGIMOTO, Takahiro; MIYAZAKI,Tohru; ODA, Tsuneo; HOASHI, Yasutaka; HATTORI,Yasushi; IMAMURA, Keisuke; (413 pag.)WO2019/27058; (2019); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 78191-00-1, name is N-Methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C4H9NO2

To a stirred solution of 5-methylthiazole 75 (9 g, 90.90 mmol) in anhydrous THF (200 mL) under inert atmosphere was added n-butyl lithium (40 mL, 99.99 mmol) dropwise for 30 min at -78 oC. To this was added N-methoxy-N-methylacetamide (11.24 mL, 109.1 mmol) dropwise for 20 min at -78 oC, followed by warming to 0 oC and stirring for 16 min. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution and extracted using EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 3% EtOAc/ hexanes to afford compound 76 (12 g, 94%) as pale yellow liquid. TLC: 10% EtOAc/ hexanes (Rf: 0.5); 1H NMR (DMSO-d6, 400 MHz): delta 7.83 (s, 1H), 2.58 (s, 3H), 2.54 (s, 3H).

According to the analysis of related databases, 78191-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASSEMBLY BIOSCIENCES, INC.; TURNER, William, W., Jr.; LI, Leping; HAYDAR, Simon, Nicolas; BURES, Mark, G.; RAI, Roopa; FRANCIS, Samson; ARNOLD, Lee, Daniel; (0 pag.)WO2018/160878; (2018); A1;,
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Electric Literature of 67442-07-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 67442-07-3 as follows.

[0541] A mixture of N-(4-chlorobenzyl)-2-(hydroxymethyl)-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide (100 mg, 0.288 mmol), potassium carbonate (60 mg, 0.43 mmol) and 2-chloro-N-methoxy-N-methylacetamide (200 mg) in DMF (1.5 mL) was shaken at room temp. for 48 hrs. The mixture was diluted with water (5 mL), and the resulting solid was collected by filtration. The crude solid was recrystallized from aq. ethanol to afford title compound (90 mg). The title compound is also a compound of formula I. [0542] Physical characteristics are as follows: [0543] 1H NMR (400 MHz, DMSO-d6) delta) 10.45 (1H), 8.73 (1H), 7.37 (4H); 7.26 (1H), 5.91 (1H), 5.47 (2H), 4.74 (2H), 4.54 (2H), 3.86 (3H), 3.16 (3H); HPLC ret time=2.86 min; MS (ES+) m/z 450, 452.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Larsen, Scott D.; May, Paul; Romines, Karen; Schnute, Mark E.; Tanis, Steven P.; US2004/138449; (2004); A1;,
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Application of 14719-21-2, The chemical industry reduces the impact on the environment during synthesis 14719-21-2, name is 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, I believe this compound will play a more active role in future production and life.

A solution of compound 57 (50 mg, 0.08 mmol), N-propargyltrifluoroacetylamide (117 mg, 0.8 mmol), tetrakis(triphenylphosphine)-palladium(0) (18 mg, 0.02 mmol), Cul (5.9 mg, 0.03 mmol), and Et3N (48 mu?, 0.34 mmol) in anhydrous DMF (3.0 mL) was stirred at 50 C for 12 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography to yield 7-{(5)-l-[5-methoxy-4-(3-trifluoroacetamido-l-propynyl)-2-nitrophenyl]-2,2-dimethyl-propyloxy}methyl-7-deaza-2′-deoxyguanosine 58 (50 mg, 96%). 1H NMR (400 MHz, MeOH-d4): delta 7.87 (s, 1 H, Ph-H), 7.26 (s, 1 H, Ph-H), 6.84 (s, 1 H, H-8), 6.20 (m, 1 H, H-l ‘), 5.25 (s, 1 H, Ph-CH), 4.67 (d, 1 H, J = 12.0 Hz, 7-CH2a), 4.54 (d, 1 H, J = 12.0 Hz, 7-CH2b), 4.43 (m, 1 H, H-3 ‘), 4.33 (s, 2 H, CH2), 3.95 (s, 3 H, OCH3), 3.89 (m, 1 H, H-4′), 3.70 (m, 2 H, H-5’), 2.46 (m, 1 H, H-2’a), 2.18 (m, 1 H, H-2’b), 0.86 (s, 9 H, (CH3)3).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2,2,2-Trifluoro-N-(prop-2-yn-1-yl)acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LASERGEN, INC.; STUPI, Brian, Philip; LI, Hong; WU, Weidong; HERSH, Megan, N.; HERTZOG, David; MORRIS, Sidney, E.; METZKER, Michael, L.; WO2013/40257; (2013); A1;,
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Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 37045-73-1, name is 3-(Methylsulfonamido)aniline, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 37045-73-1, Quality Control of 3-(Methylsulfonamido)aniline

This was prepared from 2,4-dichloro-5-methylpyrimidine (0.326 g), N-(3- aminophenyl)methanesulfonamide (0.372 g) and DIPEA (0.418 mL) using procedure B (reaction time, 48 h) and isolated in the same way as MA2-030 to give the title compound MA2-035 as a gray solid (0.374 g, 100%). Mp: 191-193 C. NMR (400 MHz, DMSO-ifc): delta 9.85 (s, 1H, disappeared on D2O shake), 8.95 (s, 1H, disappeared on D2O shake), 8.06 (d, / = 0.9 Hz, 1H), 7.54 (t, / = 1.9 Hz, 1H), 7.35 (dd, / = 8.4, 1.5 Hz, 1H), 7.30 (t, / = 8.0 Hz, 1H), 6.91 (ddd, / = 7.8, 2.0, 1.1 Hz, 1H), 3.05 (s, 3H), 2.17 (s, 3H). HPLC-MS (ESI+): m/z 315.2 [40%, (M35C137 +], 313.1 [100%, (M35C135C1+H)+]. Procedure B A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
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Amide – an overview | ScienceDirect Topics

Synthetic Route of 758-96-3, The chemical industry reduces the impact on the environment during synthesis 758-96-3, name is N,N-Dimethylpropionamide, I believe this compound will play a more active role in future production and life.

General procedure: tert-Butyl acetate (0.14 mL; 1.0 mmol) was added to a solution of LDA (1.0 mmol) in 3 mL of dry THF at -78 C under argon atmosphere with stirring. After the solution was stirred for 10 min, a solution of vinyl sulfoxide 8 (71 mg; 0.2 mmol) in THF (1 mL) was added. The reaction mixture was stirred for 15 min and then reaction was quenched by adding saturated aq. NH4Cl. The whole mixture was extracted with CHCl3. The product was purified by silica gel column chromatography to afford adduct 9 (94 mg; 99%) as colorless oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N,N-Dimethylpropionamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Satoh, Tsuyoshi; Awata, Yu; Kato, Yuichi; Ogata, Shingo; Ishigaki, Masashi; Sugiyama, Shimpei; Saitoh, Hideki; Tetrahedron; vol. 67; 6; (2011); p. 1102 – 1113;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 17193-28-1, name is 1-Amino-1-cyclopentanecarboxamide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H12N2O

6.19. Preparation of l-(4-(4-(2-nnet yl-5-((2S.3R.4R.5S.6R)-3.4.5-tririvdroxy-6- (met yltriio)tetra vdro-2H-pyran-2- yl)benzyl)prienoxy)butanannido)cvclopentanecarboxamide (41) 4-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2- yl)benzyl)phenoxy)butanoic acid (39, 46 mg, 0.10 mmol), 1-aminocyclopentanecarboxamide (26 mg, 0.20 mmol), HATU (57 mg, 0.15 mmol), and DIPEA (52 muIota_, 0.30 mmol) were combined in DMF (0.5 ml_) and stirred overnight at room temperature. The reaction was diluted with EtOAc, washed with saturated aqueous NaHC03 and brine (with back extraction), dried over MgS04, filtered, and concentrated under vacuum. The material was purified by prep HPLC (C18 30 x 100 mm column, 20-60% CH3CN /10 mM aqueous ammonium formate, 45 mL/min) and lyophilized to give 35 mg (61% yield) of amide 41 as a white solid. W NMR (400 MHz, MeOH-d4) delta ppm 7.10 – 7.19 (m, 3 H), 7.04 (d, J=8.6 Hz, 2 H), 6.81 (m, J=8.6 Hz, 2 H), 4.39 (d, J=9.3 Hz, 1 H), 4.12 (d, J=9.1 Hz, 1 H), 3.96 (t, J=6.2 Hz, 2 H), 3.92 (s, 2 H), 3.34 – 3.50 (m, 3 H), 2.41 (t, J=7.5 Hz, 2 H), 2.12 – 2.22 (m, 8 H), 2.04 (quin, J=6.9 Hz, 2 H), 1.93 (dt, J=12.8, 5.1 Hz, 2 H), 1.64 – 1.75 (m, 4 H); MS (ES+) [M+H]+ = 573.

According to the analysis of related databases, 17193-28-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEXICON PHARMACEUTICALS, INC.; CARSON, Kenneth Gordon; GOODWIN, Nicole Cathleen; HARRISON, Bryce Alden; RAWLINS, David Brent; STROBEL, Eric; ZAMBROWICZ, Brian; WO2014/81660; (2014); A1;,
Amide – Wikipedia,
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